Concentrated stock position — RSUs vested, ISOs you exercised, ESPP shares, or just an old position that grew. Enter the position + your income, see the exact tax bill, and compare 3 ways to soften it: spread the sale, gift to a DAF, or borrow against it.
Selling stock at a gain triggers a capital-gains tax. The federal rate depends on how long you held it and your income:
On top of federal, you usually owe state tax on the same gain (most states treat cap gains as ordinary income — California up to 13.3%, New York up to 10.9%, etc.). And if your MAGI is over $200k single / $250k MFJ, the 3.8% Net Investment Income Tax kicks in. Stack them all and a high earner in California can hit ~37% on long-term gains.
When RSUs vest, the full FMV is treated as W-2 wages — your employer withholds taxes (usually a flat 22% federal, which often under-withholds for high earners). That sets your cost basis to the vest-day share price.
When you later sell, only the gain ABOVE that vest-day price is a new capital gain. If you sell at vest (sell-to-cover style), the capital gain is near $0 and you've already paid the wage tax. If you held shares for years after vest, you have a meaningful long-term gain to deal with — that's what this calculator handles.
The 0% LTCG bracket goes up to $48,350 of taxable income for single filers in 2025 (about $96,700 MFJ). If you can keep your annual income + gain UNDER that, you literally pay 0% federal on long-term gains. Similarly, the 15% bracket runs up to $533,400 single — staying under that avoids the 20% top rate.
Slicing a big position into multiple years often pulls each year's stack out of the 20% bracket and below the NIIT threshold ($200k / $250k MAGI). The tradeoff: market risk while you wait, and you can't time it perfectly.
A Donor-Advised Fund (Fidelity Charitable, Schwab Charitable, Vanguard Charitable) accepts appreciated shares directly. Two benefits stack:
The catch: the money goes to charity, not back to you. This is only better than selling if you were going to donate anyway. For people who DO donate, gifting shares instead of cash is almost always the right move.
A Securities-Backed Line of Credit lets you borrow against your portfolio at prime + 0% to prime + 2% (currently ~8.5%–10.5%). The shares stay invested, no capital gain is triggered, and you have liquidity for a down payment, business, or whatever.
The risks are real:
Best fit: short-term liquidity (1-3 years) where you'd otherwise sell stock that you expect to keep growing.